Hexamethylene-tetramin-diguaiacol.



'UNIE sm as @PA EN neon.

EMIL BARELL AND FRANZ ELGER, OF BASEL, SWITZERLAND, ASSIGNORS TO THEFIRM OF THE HOFFMANN-LA-ROCHE CHEMICAL WORKS, 013 NEW YORK, N. Y.

HEXAMETHYLENE-TETRAMIN-DIGUAIAGOL.

No Drawing.

Specification of Letters Patent. Patented Dec, 27, 1910,

Application filed June 18, 1910. Serial No. 567,692.

To all whom it may concern:

Be it known that we, EMIL BARELL, a citizen of the Swiss Confederation,and FRANZ ELGER, a subject of the Austro-Hungarian Emperor, residing atBasel, Switzerland, have invented a certain new and useful Compound ofGuaiacol and Process for Obtaining the Same, of which the following is aspecification.

According to ourapplication for patent Serial No. 461,234hexa-methylene-tetramintriguaiacol is obtained, by causing guaiacol toact on hexa-methylene-tetramin in aqueous solution or by causing aformaldehydesolution to act on ammoniacal guaiacol-solution in theproportions corresponding to the compound:

sides the hexa-methylene-tetramin-triguaia- 001, there exist otherstable molecular compounds of hexa-methylene-tetramin and guaiacol. Forinstance, if 4: kilos of crystallized guaiacol are added to a warmsolution of 8 kilos of hexa-methylene-tetramin in 10 liters of water,and the mixture is heated on a boiling water bath until a clear solutionhas been formed, the subsequent cooling causes the formation of crystalsof a body, which is a hexa-methylene-tetramin-diguaiacol and correspondsto the hexa-methylene-tetramin-triguaiacol as regards its properties. Onheating, the said compound softens at first, then it melts at about9095, with 22 parts of water it yields a clear solution, it is easilysoluble in cold alcohol and in chloroform, and on being distilled in acurrent of steam it yields guaiacol equal in weight to 63.9 per cent. ofthe new compound.

For producing the new compound, the guaiacol and the hexa-methylenemayalso be caused to act upon each other in a dry condition. For instance,if 124 grams of guaiacol are ground together with 70 grams ofhexa-methylene-tetramin in a mortar the mixture assumes at first theconsistency of a broth, and then that of a thick liquid. If the grindingand stirring is continued or if the mixture is left to itself for sometime, the whole solidifies again and thehexa-methylene-tetramin-diguaiacol is obtained as a dry powder.

By varying the proportions, solid compounds are obtained whose analysesindicate, that we are dealing with mixtures ofhexamethylene-tetramin-mono-guaiacol andhexamethylene-tetramin-diguaiacol, or with mixtures ofhexa-methylene-tetramin-diguaiacol andhexa-methylene-tetramin-triguaiacol.

All these compounds may be easily split up into their components and areValuable for therapeutic purposes.

What we claim is:

1. The process for the production of hexamethylene-tetramin-diguaiacol,which consists in causing guaiacol to act on hexa-methylene-tetramin inproportions corresponding to the compound G H l- G 3)- EMIL BARELL.FRANZ ELGER.

Witnesses:

D. FISCHER, GEO. GIFFORD, A. TROENDLE, ARNOLD ZUBER.

